JP2009518362A - 高い固体含有率および低い粘度を有するエーテル化メラミン−ホルムアルデヒド縮合物 - Google Patents
高い固体含有率および低い粘度を有するエーテル化メラミン−ホルムアルデヒド縮合物 Download PDFInfo
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- JP2009518362A JP2009518362A JP2008543834A JP2008543834A JP2009518362A JP 2009518362 A JP2009518362 A JP 2009518362A JP 2008543834 A JP2008543834 A JP 2008543834A JP 2008543834 A JP2008543834 A JP 2008543834A JP 2009518362 A JP2009518362 A JP 2009518362A
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- formaldehyde condensate
- melamine
- etherified melamine
- formaldehyde
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/40—Chemically modified polycondensates
- C08G12/42—Chemically modified polycondensates by etherifying
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/40—Chemically modified polycondensates
- C08G12/42—Chemically modified polycondensates by etherifying
- C08G12/424—Chemically modified polycondensates by etherifying of polycondensates based on heterocyclic compounds
- C08G12/425—Chemically modified polycondensates by etherifying of polycondensates based on heterocyclic compounds based on triazines
- C08G12/427—Melamine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
- C08G12/30—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with substituted triazines
- C08G12/32—Melamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/30—Chemical modification by after-treatment
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
Description
(a)第一の反応工程で、メラミンをホルムアルデヒド成分により1:6〜1:15のモル比でメチロール化し、
(b)第二の反応工程で、工程(a)から得られたヒドロキシメチル化中間生成物を、C1〜C20−アルコール、有利にはC1〜C6−アルコール、および特に有利にはC1〜C4−アルコールの存在下に4.5未満のpH値でエーテル化し、
(c)第三の反応工程で、工程(b)からの反応混合物を、無機塩基の添加により9.5を上回るpH値に調整し、かつ揮発性成分、特にメタノールを、少なくとも1の蒸留工程により除去し、
(d)反応工程(b)および(c)を少なくとも1回繰り返す
ことを特徴とする、エーテル化メラミン−ホルムアルデヒド縮合物の製造方法により解決される。
Xは、メラミンのモルに相応し、
Yは、ホルムアルデヒドのモルに相応し、
Zは、メタノールのモルに相応する。
反応容器中に、40%のホルムアルデヒド水溶液375gを装入し、25%水溶液の形のNaOHによりpH値を9に調整する。メラミン70gを添加した後に、反応混合物を70℃に加熱し、かつ50℃の時点から40分間攪拌する。得られるヒドロキシメチル化中間生成物を引き続き、メタノール167gで希釈し、30%のHNO3水溶液3.2mlを用いてpH値を3に調整し、かつ60℃で30分間エーテル化する。25%NO水酸化ナトリウム溶液を2.8ml添加することにより10を上回るpH値を調整し、かつエーテル化反応を終了する。過剰のメタノールを真空下に80ミリバールの圧力および温度90℃で留去する。
1/4/4 1/5/4 1/6/4 1/5/5 1/6/5 1/6/6 1/7/6 2/X/X (モル/モル/モル)
1.7 7.4 11.9 3.9 11.5 6.4 1.8 7.1 (面積%)
置換は依然として完全ではなく、生成物の50%が把握されるのみであり、その一方で、残分は分類できないことが明らかである。
1/4/4 1/5/4 1/6/4 1/5/5 1/6/5 1/6/6 1/7/6 2/X/X (モル/モル/モル)
0.3 1.3 1.9 5 13.3 18.1 5.2 46.5 (面積%)
引き続き、生成物を再度、メタノール267gで希釈し、30%のHNO3水溶液1.2mlによりpH値を3に調整する。縮合は、温度60℃で12分間行う。引き続き該溶液を25%のNaOH水溶液0.9mlでアルカリ性に調整し、かつ過剰のメタノールを真空下に120ミリバールの圧力および温度90℃で留去する。
1/4/4 1/5/4 1/6/4 1/5/5 1/6/5 1/6/6 1/7/6 2/X/X (モル/モル/モル)
0.4 1.7 0.9 0.6 9 31.9 8 28.2 (面積%)
この例により、完全にエーテル化された生成物(1/4/4、1/5/5、1/6/6)の割合が段階的に増加し、その際、同時に反応混合物の粘度が75000mPasから6400mPasに低下することが明らかである。
Claims (9)
- エーテル化メラミン−ホルムアルデヒド縮合物の製造方法において、
(a)第一の反応工程で、メラミンをホルムアルデヒド成分により1:6〜1:15のモル比でメチロール化し、
(b)第二の反応工程で、工程(a)から得られたヒドロキシメチル化中間生成物を、C1〜C4−アルコールの存在下に4.5未満のpH値でエーテル化し、
(c)第三の反応工程で、工程(b)からの反応混合物を、無機塩基の添加により9.5を上回るpH値に調整し、かつ揮発性成分、特にメタノールを、少なくとも1の蒸留工程により除去し、
(d)反応工程(b)および(c)を少なくとも1回繰り返す
ことを特徴とする、エーテル化メラミン−ホルムアルデヒド縮合物の製造方法。 - メチロール化(a)を、7を上回るpH値で実施することを特徴とする、請求項1記載のエーテル化メラミン−ホルムアルデヒド縮合物の製造方法。
- エーテル化(b)の際に、アルコールとしてメタノールを使用することを特徴とする、請求項1または2記載のエーテル化メラミン−ホルムアルデヒド縮合物の製造方法。
- 反応工程(c)の蒸留工程の後で、無機塩基を反応混合物に計量供給して9.5未満のpH値を調整することを特徴とする、請求項1から3までのいずれか1項記載のエーテル化メラミン−ホルムアルデヒド縮合物の製造方法。
- 反応工程(c)の少なくとも1の蒸留工程を、流下薄膜式蒸発器、薄層蒸発器またはサムベイ蒸発器中で実施することを特徴とする、請求項1から4までのいずれか1項記載のエーテル化メラミン−ホルムアルデヒド縮合物の製造方法。
- 6未満の置換度を有する単環式成分の割合が、メラミン−ホルムアルデヒド縮合物の全量に対して10%を下回ることを特徴とする、請求項1から5までのいずれか1項記載の方法により製造されるエーテル化メラミン−ホルムアルデヒド縮合物。
- 固体含有率が96%を上回ることを特徴とする、請求項1から5までのいずれか1項記載の方法により製造されるエーテル化メラミン−ホルムアルデヒド縮合物。
- 粘度が3000mPasを下回ることを特徴とする、請求項1から5までのいずれか1項記載の方法により製造されるエーテル化メラミン−ホルムアルデヒド縮合物。
- 酸硬化性架橋剤としての、請求項1から5までのいずれか1項記載の方法により製造された、エーテル化メラミン−ホルムアルデヒド縮合物の使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102005058855.7 | 2005-12-09 | ||
DE102005058855A DE102005058855A1 (de) | 2005-12-09 | 2005-12-09 | Veretherte Melamin-Formaldehydkondensate mit hohem Feststoffgehalt und geringer Viskosität |
PCT/EP2006/069409 WO2007065922A1 (de) | 2005-12-09 | 2006-12-07 | Veretherte melamin-formaldehydkondensate mit hohem feststoffgehalt und geringer viskosität |
Publications (2)
Publication Number | Publication Date |
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JP2009518362A true JP2009518362A (ja) | 2009-05-07 |
JP5371438B2 JP5371438B2 (ja) | 2013-12-18 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2008543834A Expired - Fee Related JP5371438B2 (ja) | 2005-12-09 | 2006-12-07 | 高い固体含有率および低い粘度を有するエーテル化メラミン−ホルムアルデヒド縮合物 |
Country Status (11)
Country | Link |
---|---|
US (1) | US9039927B2 (ja) |
EP (1) | EP1960445B1 (ja) |
JP (1) | JP5371438B2 (ja) |
KR (1) | KR101390622B1 (ja) |
CN (1) | CN101326210B (ja) |
DE (1) | DE102005058855A1 (ja) |
DK (1) | DK1960445T3 (ja) |
ES (1) | ES2456416T3 (ja) |
PL (1) | PL1960445T3 (ja) |
SI (1) | SI1960445T1 (ja) |
WO (1) | WO2007065922A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20140085457A (ko) * | 2011-10-21 | 2014-07-07 | 올넥스 아이피 에스에이알엘 | 아미노플라스트 가교제 수지 조성물, 그 제조 방법 및 사용 방법 |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2155803A1 (de) * | 2007-06-05 | 2010-02-24 | Basf Se | Hochverzweigte melaminpolymere |
CN101619126B (zh) * | 2009-07-31 | 2010-12-08 | 常州曙光化工厂 | 橡胶用三聚氰胺甲醛树脂的制备方法 |
CN101817914B (zh) * | 2010-05-11 | 2012-05-23 | 辽宁恒星精细化工(集团)有限公司 | 一种低游离甲醛甲醚化三聚氰胺甲醛树脂交联剂的合成方法 |
US20140326672A1 (en) * | 2011-11-29 | 2014-11-06 | Agency For Science, Technology And Research | Melamine aldehyde polymers |
CN103641970B (zh) * | 2013-12-04 | 2015-07-29 | 中国林业科学研究院林产化学工业研究所 | 一种高固含三聚氰胺甲醛基树脂的制备方法 |
CN106318353A (zh) * | 2015-06-15 | 2017-01-11 | 中石化石油工程技术服务有限公司 | 一种凝胶堵漏剂及其制备方法 |
CN110099940A (zh) | 2016-12-21 | 2019-08-06 | 巴斯夫欧洲公司 | 制备醚化蜜胺甲醛树脂的液体组合物的方法 |
KR102192059B1 (ko) * | 2020-03-19 | 2020-12-17 | 태림산업(주) | 방화 보온 재료의 발포 성형방법 |
CN111440282A (zh) * | 2020-06-09 | 2020-07-24 | 重庆建峰浩康化工有限公司 | 甲醚化氨基树脂的环保生产方法 |
CN112126031A (zh) * | 2020-10-20 | 2020-12-25 | 句容宁武新材料股份有限公司 | 一种低碳醇体系下三聚氰胺甲醛树脂的合成方法 |
CN114920708B (zh) * | 2022-05-27 | 2024-02-13 | 山东阳谷华泰化工股份有限公司 | 一种六羟甲基三聚氰胺的连续化生产方法 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2998411A (en) * | 1958-03-17 | 1961-08-29 | American Cyanamid Co | Melamine-formaldehyde reaction products and process of preparing the same |
GB1030268A (en) * | 1963-11-27 | 1966-05-18 | American Cyanamid Co | Polymethyl ethers of hexamethylol melamine |
JPS5312883A (en) * | 1976-07-19 | 1978-02-04 | American Cyanamid Co | Production of novev methyl methylol melamine composition |
US4223141A (en) * | 1978-09-13 | 1980-09-16 | Cassella Aktiengesellschaft | Preparation of methoxy-methyl melamines |
JP2003523424A (ja) * | 2000-02-15 | 2003-08-05 | ソリユテイア・インコーポレイテツド | アルコキシメチルメラミン架橋剤 |
WO2005068441A1 (de) * | 2004-01-19 | 2005-07-28 | Basf Aktiengesellschaft | Kontinuierliches verfahren zur herstellung von hochmethyloliertem melamin und veretherten melaminformaldehydharzen |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2516349C3 (de) | 1975-04-15 | 1981-03-19 | Cassella Ag, 6000 Frankfurt | Verfahren zur Herstellung von verätherten Methylol-melaminen und -benzoguanaminen |
US4183832A (en) * | 1975-04-30 | 1980-01-15 | Saint-Gobain Industries | Aqueous solutions of etherified melamine-formaldehyde resins with long shelf life and low free formaldehyde content |
US4425466A (en) * | 1981-09-09 | 1984-01-10 | Monsanto Company | Coating compositions comprising a methylated methylolated melamine |
DE3216927A1 (de) | 1982-05-06 | 1983-11-10 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von faeden und fasern, die zu mindestens 80 gew.% aus melamin-formaldenhydkondensaten bestehen |
DE3905913A1 (de) * | 1989-02-25 | 1990-09-13 | Basf Ag | Aminoharz-loesungen mit geringer elektrischer leitfaehigkeit |
DE10007951A1 (de) | 1999-03-23 | 2000-09-28 | Basf Ag | Melaminharze |
DE10261804B4 (de) * | 2002-12-19 | 2008-05-21 | Ami-Agrolinz Melamine International Gmbh | Direktsyntheseverfahren zur Herstellung von veretherten Melaminharzkondensaten, Melaminharzkondensate und deren Verwendung |
DE102005025898A1 (de) | 2005-06-06 | 2006-12-07 | Basf Ag | Verfahren zur Rückgewinnung von Wertstoffen aus Strömen, die bei der Aufkonzentrierung von Alkoxycarbonylaminotriazin enthaltenden Reaktionsgemischen anfallen |
DE102005025901A1 (de) | 2005-06-06 | 2006-12-07 | Basf Ag | Verfahren zur Aufbereitung eines Alkoxycarbonylaminotriazin enthaltenden Reaktionsgemisches |
DE102005036584A1 (de) | 2005-08-01 | 2007-02-15 | Basf Ag | Gemischtveretherte Melamin-Formaldehyd-Harze |
EP2155803A1 (de) | 2007-06-05 | 2010-02-24 | Basf Se | Hochverzweigte melaminpolymere |
-
2005
- 2005-12-09 DE DE102005058855A patent/DE102005058855A1/de not_active Withdrawn
-
2006
- 2006-12-07 KR KR1020087016213A patent/KR101390622B1/ko active IP Right Grant
- 2006-12-07 SI SI200631757T patent/SI1960445T1/sl unknown
- 2006-12-07 DK DK06830434.4T patent/DK1960445T3/da active
- 2006-12-07 US US12/096,502 patent/US9039927B2/en active Active
- 2006-12-07 CN CN200680046023XA patent/CN101326210B/zh active Active
- 2006-12-07 JP JP2008543834A patent/JP5371438B2/ja not_active Expired - Fee Related
- 2006-12-07 PL PL06830434T patent/PL1960445T3/pl unknown
- 2006-12-07 WO PCT/EP2006/069409 patent/WO2007065922A1/de active Application Filing
- 2006-12-07 EP EP06830434.4A patent/EP1960445B1/de active Active
- 2006-12-07 ES ES06830434.4T patent/ES2456416T3/es active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2998411A (en) * | 1958-03-17 | 1961-08-29 | American Cyanamid Co | Melamine-formaldehyde reaction products and process of preparing the same |
GB1030268A (en) * | 1963-11-27 | 1966-05-18 | American Cyanamid Co | Polymethyl ethers of hexamethylol melamine |
JPS5312883A (en) * | 1976-07-19 | 1978-02-04 | American Cyanamid Co | Production of novev methyl methylol melamine composition |
US4223141A (en) * | 1978-09-13 | 1980-09-16 | Cassella Aktiengesellschaft | Preparation of methoxy-methyl melamines |
JP2003523424A (ja) * | 2000-02-15 | 2003-08-05 | ソリユテイア・インコーポレイテツド | アルコキシメチルメラミン架橋剤 |
WO2005068441A1 (de) * | 2004-01-19 | 2005-07-28 | Basf Aktiengesellschaft | Kontinuierliches verfahren zur herstellung von hochmethyloliertem melamin und veretherten melaminformaldehydharzen |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20140085457A (ko) * | 2011-10-21 | 2014-07-07 | 올넥스 아이피 에스에이알엘 | 아미노플라스트 가교제 수지 조성물, 그 제조 방법 및 사용 방법 |
KR102000801B1 (ko) | 2011-10-21 | 2019-07-16 | 알넥스 네덜란드 비. 브이. | 아미노플라스트 가교제 수지 조성물, 그 제조 방법 및 사용 방법 |
Also Published As
Publication number | Publication date |
---|---|
US9039927B2 (en) | 2015-05-26 |
KR20080080609A (ko) | 2008-09-04 |
PL1960445T3 (pl) | 2014-08-29 |
EP1960445A1 (de) | 2008-08-27 |
WO2007065922A1 (de) | 2007-06-14 |
CN101326210B (zh) | 2013-04-03 |
CN101326210A (zh) | 2008-12-17 |
US20090121181A1 (en) | 2009-05-14 |
DK1960445T3 (da) | 2014-06-10 |
ES2456416T3 (es) | 2014-04-22 |
DE102005058855A1 (de) | 2007-06-14 |
KR101390622B1 (ko) | 2014-04-29 |
SI1960445T1 (sl) | 2014-04-30 |
EP1960445B1 (de) | 2014-03-12 |
JP5371438B2 (ja) | 2013-12-18 |
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